Synthesis and atropisomerism of meso-tetraarylporphyrins with mixed meso-aryl groups having ortho-substituents

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meso-Tetraarylporphyrins having two kinds of ortho-substituted meso-aryl groups alternately at 5-, 10-, 15-, and 20-positions have been prepared by way of the modified MacDonald [2+2]-type condensation of α,α′-free aryldipyrrylmethanes with aryl aldehydes. 5,15-Di(2-acetylaminophenyl)-10,20-di-1-(2-methoxynaphthyl)porphyrin was prepared by way of two different combinations of aryldipyrryl-methanes and aryl aldehydes. The five atropisomers (αα′ββ′, αα′βα′, αβ′αβ′, αα′αβ′, αα′αα′) expected for these porphyrins were separated and characterized on the basis of the 1H NMR spectra and thermal isomerization behavior.